Novel compounds, pharmaceutical compositions containing same, and methods of use for same

Abstract

The class compounds of the present invention may be represented by Formula (I), wherein X may be O, S, or N. R 1 and R 2 are independently either H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl. R 3 and R 4 are independently either H, an aryl group, a heteroaryl group, and a heterocyclic ring group having 4 to 6 carbon atoms, wherein the aryl, heteroaryl, and heterocyclic moieties are optionally substituted with one or more of a first substitution group defined herein. In a further embodiment, R 3 and R 4 along with the atoms and bonds to which they are attached, form an optionally substituted 5-7 membered ring having at least one nitrogen atom within the ring structure.

1 . A compound comprising the formula: 
       
         
           
           
               
               
           
         
         wherein X is a heteroatom selected from the group consisting of O, S, and N; 
         R 1  and R 2  are independently selected from the group consisting of H, C 1 -C 20  alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, and alkylaryl; and 
         R 3  and R 4  are independently a hydrogen or a member of a substituted or unsubstituted ring having 4-6 carbon atoms, provided that both R 3  and R 4  are not hydrogens and further that, if neither R 3  and R 4  are hydrogens, then R 3  and R 4  are members of the same substituted or unsubstituted ring having 4-6 carbon atoms. 
       
     
     
         2 - 77 . (canceled) 
     
     
         78 . The compound of  claim 1 , wherein X is either an oxygen or sulfur. 
     
     
         79 . The compound of  claim 1 , wherein R 3  is a hydrogen and R 4  is selected from the group consisting of a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted heterocyclic ring group each having 4-6 carbon atoms. 
     
     
         80 . The compound of  claim 79 , wherein R 4  is substituted with one or more of a first substituent group selected from the group consisting of a halogen atom, a C 1 -C 3  alkyl group, a C 1 -C 3  haloalkyl group, —OR 5 , —SR 5 , —CN, —CONH 2 , —SO 2 NH 2 , —C(O)OR 6 —CONHR 7  and a cycloalkyl or a heterocyclic ring, wherein the cycloalkyl or heterocyclic ring of the first substituent group is optionally aromatic, is optionally fused to two adjacent atoms of R 4 , and is optionally substituted with at least one substituent group comprised of R 5 ,
 wherein R 5  is selected from the group consisting of a C 1 -C 8  alkyl, C 1 -C 8  alkoxy, aryl, alkylaryl, and arylalkyl, and is optionally substituted with one or more of a second substituent group selected from the group consisting of a halogen atom, a C 1 -C 3  alkyl group, a C 1 -C 3  alkoxy group, a C 1 -C 3  haloalkyl group, and a C 1 -C 3  haloalkoxy group, 
 wherein R 6  is comprised of a C 1 -C 8  alkyl group and R 7  is selected from the group consisting of a C 1 -C 8  alkyl group, an allyl group, a morpholine, a piperazine, an N-substituted piperazine with R 5 , and a 5- or 6-membered heterocycle containing N, O, S or any combination thereof. 
 
     
     
         81 . The compound of  claim 80 , wherein R 3  is a hydrogen and R 4  is an aryl group optionally substituted with one or more of the first substituent group. 
     
     
         82 . The compound of  claim 1 , wherein R 1  is a straight or branched chain C 6 -C 8  alkyl group. 
     
     
         83 . The compound of  claim 1 , wherein R 1  is a straight or branched chain C 8  alkyl group. 
     
     
         84 . The compound of  claim 1 , wherein R 2  is a straight or branched chain C 1 -C 3  alkyl group. 
     
     
         85 . The compound of  claim 1 , wherein R 2  is a methyl group. 
     
     
         86 . A compound comprising the formula: 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are independently selected from the group consisting of H, C 1 -C 20  alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, and alkylaryl; and 
         R 3  and R 4  are independently a hydrogen or a member of a substituted or unsubstituted ring having 4-6 carbon atoms, provided that both R 3  and R 4  are not a hydrogen and further that, if neither R 3  and R 4  are hydrogens, then R 3  and R 4  are members of the same substituted or unsubstituted ring having 4-6 carbon atoms. 
       
     
     
         87 . A compound of  claim 86 , wherein said compound is selected from the group consisting of 
       
         
           
           
               
               
           
         
       
     
     
         88 . A pharmaceutical composition comprising a pharmaceutical diluent and a compound according to  claim 1 . 
     
     
         89 . The pharmaceutical composition of  claim 88 , wherein X is sulfur. 
     
     
         90 . The pharmaceutical composition of  claim 88 , wherein R 1  is a straight or branched chain C 6 -C 8  alkyl group and R 2  is a straight or branched chain C 1 -C 3  alkyl. 
     
     
         91 . The pharmaceutical composition of  claim 88 , wherein R 3  is a hydrogen and R 4  is an aryl group optionally substituted with one or more of the first substitution group. 
     
     
         92 . The pharmaceutical composition of  claim 89 , wherein the compound is selected from the group consisting of 
       
         
           
           
               
               
           
         
       
     
     
         93 . A method of treating cancer, inducing weight loss, inhibiting growth of invasive microbial cells, or inhibiting fatty acid synthase activity in a subject, comprising administering to the subject an effective amount of a pharmaceutical composition according to  claim 88 . 
     
     
         94 . The method of  claim 93 , wherein the method comprises treating cancer. 
     
     
         95 . The method of  claim 93 , wherein the subject is an animal. 
     
     
         96 . The method of  claim 95 , wherein the subject is a human. 
     
     
         97 . The method of  claim 93 , wherein X is sulfur. 
     
     
         98 . The method of  claim 93 , wherein R 1  is a straight or branched chain C 6 -C 8  alkyl group and R 2  is a straight or branched chain C 1 -C 3  alkyl. 
     
     
         99 . The method of  claim 93 , wherein R 3  is a hydrogen and R 4  is an aryl group optionally substituted with one or more of the first substituent group. 
     
     
         100 . The method of  claim 93 , wherein the pharmaceutical composition includes one or more compounds selected from the group consisting of: